Vacation Home Rentals By Owner In Chicago, IL

Showing 220 Of 354 Vacation Rentals

$283.38

Beautiful home near WhiteSox Stadium and Downtown Chicago.

Chicago, Illinois, United States

Experience comfort and convenience in our newly renovated Georgian Style home. With 3 spacious bedrooms, 2 full bathrooms, an open concept kitchen, and a backyard deck, there's plenty of room to relax and unwind. Stay entertained with 4 Smart/Roku TVs and Wi-Fi throughout the home. For your safety, we have a exterior cameras and a security system that you can arm and disarm. Our home is conveniently located near the highway, shopping center, and restaurants. Book your stay now!

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Sleeps

$278.03

/ Nightly

Private Vacation Home

Spacious Home Away From Home

Chicago, Illinois, United States

RUN, DON'T WALK. Bring the whole family to this spacious elegant 4,500 square feet home with main level theatre room, fully equiped office with T.V. for gamers and LED lighted bedrooms. All other living areas are equally well appointed with stainless steel kitchen appliances and cabnet space to feed a army. Second floor master suite with jacuzzi deep tub and king size bed with all the extras, including a walk-in closet. Outside amenities include wroughtiron fence, private backyard patio, and Blink security system. Plenty of free parkng and only 0.2 miles from public transportation. 75 inch television in theatre room with surroundsound and LED lighting. Central air, outside cameras, and plenty of closet space for clothing. There is loads more to see; so hurry and book your stay today.

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Sleeps

Exceptional(2)

$319.36

/ Nightly

Private Vacation Home

2 Mi to South Shore Beach: Urban Retreat w/ Yard

Chicago, Illinois, United States

Deck w/ Outdoor Dining Area | 1 Mi to Metra Station | 3 Mi to UChicago: Hyde ParkbrbrMake the most of your Windy City retreat and book this 3-bedroom, 2-bath Chicago vacation rental! The townhome features an updated interior, a fully stocked kitchen, and a private outdoor space perfect for morning coffee and quiet evenings. Visit South Shore Beach and make a splash in Lake Michigan, or take nearby public transit downtown for shopping, museum-hopping, and live entertainment!brbr-- THE PROPERTY --brbrR25000131811brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bedbr- Living Room: 1 queen sleeper sofabrbrINDOOR LIVINGbr- 4 Smart TVsbr- 2 laptop workspaces, booksbr- Dining tablebrbrOUTDOOR LIVINGbr- Deck w/ dining areabr- Fenced backyard w/ addt’l seating brbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Dishware/flatware, cooking basics, spicesbr- Drip coffee makerbr- Microwave, toasterbrbrGENERALbr- Free WiFibr- Keyless entrybr- Central A/C & heating, ceiling fansbr- Linens/towels, iron/boardbr- Washer/dryer (detergent provided)br- Trash bags, paper towelsbr- Hair dryer, complimentary toiletriesbrbrFAQbr- Quiet hours (8:00 PM-8:00 AM)br- 3 exterior security cameras (facing out)brbrACCESSIBILITYbr- 2-story townhome w/ basement, exterior stairs requiredbr- No 1st-floor bedrooms or full bathroomsbrbrPARKINGbr- Free street parking (first-come, first-served)brbr-- THE LOCATION --brbr- Nestled in the Jackson Park Highlands neighborhoodbr- 1 mile to Stony Island Metra Stationbr- 2 miles to South Shore Beach & Lake Michiganbr- 2 miles to Jackson Parkbr- 2 miles to Griffin Museum of Science and Industrybr- 9 miles to downtown Chicago: Grant Park, Shedd Aquarium, Field Museum, Soldier Field, shops, restaurants, bars, live entertainmentbr- 15 miles to Chicago Midway International Airport & 26 miles to Chicago O'Hare International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- Please observe quiet hours from 8:00 PM to 8:00 AMbrbrADDITIONAL INFORMATIONbr- Your safety matters. This property features 3 exterior security cameras next to the front, side, and back doors facing the sidewalk, street, side yard, and backyard. These cameras are outward facing and do not look into any interior spaces. They record video when activated by motionbr- This 2-story townhome with a basement requires exterior stairs to enter; all bedrooms and full bathrooms are on the 2nd floor or in the basement

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Bath

Sleeps

$193.47

/ Nightly

Private Vacation Home

Stylish and Cozy 2BR, Family Friendly, Free Parking

Chicago, Illinois, United States

Welcome to this beautifully remodeled, modern 2-bedroom, 1-bathroom apartment, perfectly situated in the lively and diverse Belmont & Cragin neighborhood. Nestled on a quiet, family-friendly block, this home offers the best of both worlds—a vibrant community atmosphere with a peaceful retreat to relax and unwind.

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Bath

Sleeps

Exceptional(4)

$1006.25

/ Nightly

Private Vacation Home

Modern, Luxe, House 20mins to Downtown, Private Rooftop, 2car Garage

Chicago, Illinois, United States

Luxurious Modern Retreat with 1000 sqft RooftopbrbrWelcome to the Monticello - our stunning modern new construction, designed for the ultimate luxury and comfort. This spacious retreat boasts five bedrooms each with its own bathroom, three living spaces, and a rooftop terrace offering breathtaking views of the city skyline.brbrSpacious thoughtful amenities throughout, including modern and equipped kitchen, king and queen size beds, spa bathrooms, comfortable furnishings, crib, pack and play and four flat screen TVsbrbrLocated in the vibrant neighborhood of Humboldt Park, just 5 miles from downtown Chicago, our home provides easy access to the city's top attractions, dining, and entertainment options. Please note that while our neighborhood is vibrant and full of character, it is still in an establishing and up and coming area, and guests should be mindful of safety concerns (as is the case anywhere in Chicago).brbrAll these, topped off with a two car private garage to store your vehicles.brbr

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Bath

Sleeps

Exceptional(40)

$531.35

/ Nightly

Private Vacation Home

Historic 1920s Private Bungalow Near Logan Square, pool and beach

Chicago, Illinois, United States

Before every reservation this home is Professionally CLEANED and SANITIZED thoroughly from top to bottom. brThe only room that is not part of the listing is my personal office which is and shall remain locked on the main level to the left of the front door. brOur single family brick city Bungalow home oozes Chicago style and charm. It was completely rehabbed in 2016 and every single thing down to the mattresses, furniture and towels are brand-new in 2018. Our home has high speed internet perfect for doing work or online learning! It's a great space for a family trip, a wedding, business travelers or a couple looking for some some romance or excitement in the Windy City! The 2 bedrooms on the 2nd floor each have a brand new bedroom set and the smallest bedroom is on the main level with a twin/trundle bed combo. There is a garage that has a party door and inside garage there is a grill, dartboard, tiki bar and space for 1 car. The deck has a patio set that sits 8 and there is an outdoor fire pit. There are security cameras and an alarm on the home for peace of mind. brbrWe are close to public transportation and downtown and minutes away from the most happening Chicago neighborhoods of Logan Square, Wicker Park and the famous Lakeview ~Home of the Cubs! My home is in the HEART of Chicago in a diverse and quiet neighborhood but on the edge of excitement!brbrNo locals no parties no guests under the age of 25 unless prior approval by me. After every booking a copy of your identification is required before checking in.brbrPlease note- There are exterior video cameras only on my property for your protection and mine. brAs with every home there are always occasional power outages. I am Not responsible for the occasional power electric or Internet outage that may occur. Also, If there is a problem with the home or an issue upon check-in I must be notified immediately within 24 hours and given a chance to correct the problem. Thank you

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Sleeps

$1058.95

/ Nightly

Private Vacation Home

NEW! Spacious 3-Bed West Loop Townhouse, 1 Car Garage by AllSet Turnover

Chicago, Illinois, United States

Immerse yourself in this stylish 3 bed, 2.5 bath luxury townhouse in Chicago’sbrbrvibrant West Loop. You’re steps away from Restaurant Row with world-classbrbrdining, bars and boutiques, plus easy access to Fulton Market and downtown.brbrEnjoy an open-concept living area, sleek kitchen, private outdoor spaces andbrbrparking. Perfect for families, groups or business travelers seeking comfortbrbrand convenience in Chicago’s trendiest neighborhood. Don’t miss out-book nowbrbrand plan your next Windy City adventure! brbrGeneral Policies: brbr brbrGuest Age Policy – Guests aged 18-24 may book on an exception basis. Pleasebrbrinclude your age, reason for booking, and who will be staying with you in yourbrbrinquiry. brbr brbrLocal Guest Policy – Local guests are permitted to book on an exception basisbrbronly. Parties, gatherings, and group events are strictly prohibited.brbrUnauthorized gatherings or events will result in termination of reservationbrbrwithout refund. brbr brbrPrimary Guest Responsibility – The booking guest must stay for the fullbrbrduration and is responsible for all guests. If booking on behalf of someonebrbrelse, please contact us to discuss exceptions. brbr brbrParking – Street parking may be available but is not guaranteed. Read allbrbrposted signs to avoid tickets or towing. To secure a spot, use parking appsbrbrlike SpotHero or ParkWhiz. brbr brbrCity Noise – Some ambient noise is part of city living. brbrTAX ID: R25000129776brbrbrbr

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Sleeps

$409.04

/ Nightly

Private Vacation Home

ConerStone House

Chicago, Illinois, United States

Discover the beauty of Chicago from this marvelous 4-bedroom house. Guests will find three queen beds and one twin bed, perfect for families or groups. With three bathrooms featuring showers and hair dryers, everyone can enjoy a soothing start to their day. The house stays comfortable year-round with heating and AC, making it a brilliant retreat no matter the season.Its only a 5-minute drive to the beautiful Lake Michigan shoreline.brbrWhether you're visiting for business, family time, or a relaxing getaway, this spacious home offers comfort, convenience, and a calm atmosphere you’ll truly appreciate.

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Sleeps

Exceptional(2)

$246.89

/ Nightly

Private Vacation Home

Chicago Home Near Navy Pier & Shedd Aquarium!

Chicago, Illinois, United States

Experience the sights and sounds of Chicago when you stay at this 3-bedroom, 1-bathroom vacation rental! With its inviting interior, outdoor entertainment space, and close proximity to local attractions, this home has everything you’ll need for a worry-free getaway. Spend your days visiting animals at the Lincoln Park Zoo, picnicking at Millennium Park, or exploring Navy Pier. After a fun-filled day in the city, return home to enjoy a homemade meal with your loved ones and relax by the TV!brbr-- THE PROPERTY --brbrR24000118894 | Free WiFi | Washer & Dryer | Fenced-In Yard brbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: FutonbrbrHOME FEATURES: Flat-screen TV, 2 dining tables, laptop-friendly workspace, shower/tub combobrKITCHEN: Stove/oven, refrigerator, cooking basics, dishware/flatware, coffee maker, microwave, blenderbrGENERAL: Central air conditioning, hangers, linens/towels, trash bags/paper towelsbrFAQ: 1 exterior step required, single-story interior, 2 exterior security cameras (facing out)brPARKING: Street parking (first-come, first-served basis)brbr-- THE LOCATION --brbrATTRACTIONS: Chicago State University (1 mile), Museum of Science and Industry, Chicago (6 miles), Jackson Park (7 miles), Adler Planetarium (12 miles), Shedd Aquarium (12 miles), Millennium Park (13 miles), Skydeck Chicago (13 miles), Navy Pier (14 miles), Lincoln Park Zoo (16 miles)brWATER ACTIVITIES: Chicago Electric Boat Company (14 miles), Chicago Cycleboats (14 miles), Kayak Chicago (15 miles), Lake Katherine Kayaking (20 miles), Lake Park Boating & Sailing (30 miles)brSHOPPING SPREE: 87th Street Center (2 miles), Stony Island Plaza (2 miles), Jeffery Plaza (5 miles), Evergreen Plaza Shopping Center (5 miles), Hyde Park Shopping Center (6 miles), Grand Boulevard Plaza (6 miles)brAIRPORT: O’Hare International Airport (29 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowedbr- No events, parties, or large gatherings. This is strictly enforcedbr- Additional fees and taxes may apply br- Photo ID may be required upon check-inbr- NOTE: The property has a strict max occupancy of 6br- NOTE: The property requires 1 exterior step to enter br- NOTE: Your safety matters. This property features 2 exterior security cameras: 1 camera is located by the front entrance facing the outdoor entryway, and 1 camera is located by the back entrance facing the outdoor entryway. The cameras are outward facing and do not look into interior spaces. The cameras actively record video while guests are in residence

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Sleeps

$174.66

/ Nightly

Private Vacation Home

Furnished 2-Bed, 1.5-Bath Home – Old Irving Park – Perfect for Longer Stays!

Chicago, Illinois, United States

Looking for a cozy, fully furnished home base in Chicago without the platform mark-ups This charming single-family house blends the warmth of a neighborhood stay with the conveniences of a full home—ideal for travelers, professionals on assignment, or families needing a temporary spot.brbrYou’ll Love:br++Convenient Transit: Walk to Metra or Blue Line; only 30 minutes to downtown or O’Hare.br++Classic Chicago Vibe: 4-Square design with curated native gardens, front and back porches for coffee, reading, or open-air dining.br++Easy Parking: Garage plus ample street parking—rare for Chicago.br++Family-Friendly & Peaceful: Safe block, friendly neighbors, nearby school.br++Flexible Living: King-bed master with walk-in closet; office/second bedroom with pull-out sofa; upstairs full bath plus downstairs half bath.br++Remote Work Ready: Dedicated workspace upstairs plus an extra desk in the kitchen area.br++Cook’s Kitchen: Fully stocked and brand-new refrigerator—perfect for cooking fresh meals.br++All Comforts of Home: Central heat and A/C, laundry and storage in basement.brbrLooking for 4–6 months stay starting winter.brbrWill remove all personal items.brbrReach out for more details.

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$182.47

/ Nightly

Private Vacation Home

2 Mi to Red Line: Chicago Home Near Sherman Park

Chicago, Illinois, United States

New Kitchen Appliances | Dogs Allowed w/ Fee | Security System | 8 Mi to Grant ParkbrbrEnjoy easy access to top Chicago attractions from this spacious vacation rental! The 5-bedroom, 1.5-bath home has everything you need for an extended stay in the city, including free WiFi, a well-equipped kitchen, and a convenient location just 2 miles from the Red Line. The train will take you to spots like McCormick Place and Grant Park! In the evening, order takeout and relax with a movie on the Smart TV.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 full bedbr- Bedroom 3: 1 full bedbr- Bedroom 4: 1 twin bedbr- Bedroom 5: 1 queen bedbr- Additional Sleeping: 1 full floor mattress, 1 queen air mattressbrbrHOME FEATURESbr- Smart TVbr- Private yard (unfenced)brbrKITCHENbr- Refrigerator, stove/ovenbr- Drip coffee pot, blender, microwavebr- Cooking basics, dishware & flatwarebrbrGENERALbr- Free WiFibr- Central heatingbr- Linens & towelsbr- Complimentary toiletries, hair dryer, hangersbrbrFAQbr- 2 exterior security cameras (facing out) br- Pet fee (paid pre-trip)br- No air conditioningbr- Quiet hours (8:00 PM-8:00 AM)brbrACCESSIBILITYbr- Stairs required for entry, 2-story homebr- 2nd-floor bedroombrbrPARKINGbr- Free street parking (4 vehicles max)brbr-- THE LOCATION --brbr- 1 block to Sherman Parkbr- 2 miles to 47th Red Line Stationbr- 3 miles to the University of Chicago, DuSable Black History Museumbr- 6 miles to McCormick Placebr- 8 miles to Shedd Aquariumbr- 9 miles to Millenium Parkbr- 5 miles to Midway Int’l Airport & 24 miles to O’Hare Int’l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $100 fee (+ fees & taxes, dogs only, 2 max)br- No events, parties, or large gatheringsbr- Must be at least 19 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- Please observe quiet hours from 8:00 PM to 8:00 AMbrbrADDITIONAL INFORMATIONbr- This 2-story home requires stairs for entry and interior stairs to access the 2nd-floor bedroombr- This property does not have air conditioning br- Your safety matters. This property features 2 exterior security cameras: camera 1 is a wide-angle doorbell camera facing the street, and camera 2 is on the back facing the side street/backyard. The cameras do not look into any interior spaces. The cameras actively record video and soundbr- This property features a motion-sensor security system inside the home. These devices do not record sound or video. If triggered, the alarm will notify the local police department. Information for using the system will be provided after booking

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Bath

Sleeps

$489.57

/ Nightly

Private Vacation Home

Chic 3-bedroom building with fitness room and AC in wonderful Chicago

Chicago, Illinois, United States

Discover the beauty of Chicago from this brilliant 3-bedroom building. Each bedroom features a comfortable queen bed, perfect for a good night's sleep. With amenities like a fitness room, hair dryer, and AC, guests will feel right at home. The 2 bathrooms are equipped with all the essentials. Enjoy all that Chicago has to offer when you stay at our place.

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Bath

Sleeps

Exceptional(8)

$1360.22

/ Nightly

Private Vacation Home

Huge & Luxurious Logan Sq home,2 car garage,PRIVATE rooftop deck,great location!

Chicago, Illinois, United States

Look no further than our newly renovated house in Logan Square! Start your adventure in Chicago from this prime location in the city's northwest side. This neighborhood is known for its restaurants, coffee shops, & music venues. Once you are ready to unwind, come back and enjoy our peaceful retreat.brFeaturing:brLuxury mattresses in all rooms (4 Saatva, 1 Leesa, 1 Casper)brPrivate rooftop deckbr2 car garagebrHigh speed internet,400 mbpsbr2 of the 5 bedrooms are on the ground floor, for easy accessbrPremium linens (Pottery Barn & West Elm duvets, cotton sheets and towels, etc)brA range AND a wall oven for cooking brbr

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Sleeps

Exceptional(6)

$1838.55

/ Nightly

Private Vacation Home

Entire house w/ free parking, close to Wrigley!

Chicago, Illinois, United States

We are located in prime Lakeview location, minutes to Wrigley Field, Lincoln Park, and downtown Chicago. Lakeview Chicago is one of the most coveted areas in Chicago. While close to these top visited areas, we are also on a quiet street in one of the most safest neighborhood.brbrThis listing is for the entire house and it includes 2 covered garage parking spaces!brbr5 bedroom +office, 3.5 bathroom house full of amenities for you to enjoy! We have a pool table, arcade games, keyboard piano, record player, backyard patio deck, dry bar and games for everyone to enjoy!brbr***Living Arrangements are as followed:br1) Second floor Master Bedroom: King size bed with full size bath. There is a 55 inch TV. Full bath includes a jacuzzi. This room also has an air mattress if needed.brbr2) Second Floor Bedroom #2: King size bed . 55 Inch TV. Lounge chair that can be converted to a bed. Portable crib.brbr3) Second Floor Bedroom #3: King size bed with a 55 inch TV.brbr4) Basement Bedroom #4: Queen size bed decorated in cubs decorsbrbr5) Basement Bedroom #5: Queens size bedbrbr***Garage and ParkingbrOur garage is a covered, detached, two car garage. Please note that it is a SMALL two car garage, meaning it can likely only fit one big vehicle or two small vehicles. Please take that into consideration. There are ample metered parking nearby.brbr***Backyard Patio:brThe top patio has a swingable chair and table for those that want to sit outdoors and enjoy the weather!brbrThe bottom patio has a full patio seating, proprane grill, and outdoor games. The grill is a proprane grill. (Please note that we provide the grill and utensil set, but YOU MUST BRING YOUR OWN PROPANE IF YOU WANT TO USE THE GRILL)brbr***Kitchen:brWe have a fully stocked kitchen. We provide salt, pepper, olive oil and sugar. Cookware, bakeware, plates, cups, and utensils. Appliance list include: microwave, Keurig that allows for k-cups and filtered coffee, electric kettle for hot water, blender and toaster. If you have any questions about what we supply, please let us know.brbr***LaundrybrWasher and dryer is included and located on the second floor. We provide laundry detergent and dryer sheets. We also have an iron and ironing board!brGuest accessbrGuests have access to the whole home except for the owner’s closet in the master’s bedroom.brOther things to notebr**Internet/Technology:brFast, free wifi throughout the home! Smart TVs throughout the home. We use electronic locks, so you can enter the home with just a code! There is a total of 6 TVs in the home. Three of the TVs are 55 inch and are located in the upstairs bedrooms. The other three TVs are 65 inch in the dining room, 65 inch in the living room, and 65 inch in the basement.brbr**No pets allowed!br**No smoking allowed!br**No large parties!brbr**We have three security cameras. One outside of the front entrance, one in front of the back entrance, and one in front of the back bottom entrance that actively records video and sound. The cameras are not monitored unless there is a concern. There are no cameras inside the unit. There is an ADT system inside the home that is for security. It does not monitor video or sound. It is required that I disclose this in my listing.

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Sleeps

Exceptional(21)

$609.01

/ Nightly

Private Vacation Home

Amazing & Spacious 3 bed / 2 Bath Townhome Near Downtown, Steps from the train!

Chicago, Illinois, United States

Urban Oasis in the hearth of the city enough space for the full Family! Amazing 3 level Spacious Townhome with gated front patio and an additional private deck off the Master Bedroom on the 3rd level. Enjoy 1900 square feet of space. Home has 3 full bedrooms, a Master with King size bed and ensuite bathroom and 2 other bedrooms with a Queen bed each and a second full bathroom perfect for a family. Located in the Hearth of Lincoln Park just half a block from the CTA Train station, North and Clyborne red line station. Amenities include full washer and dryer, central AC, fireplace, fast internet WiFi, 65 inch smart TV, multiple coffee makers all in the perfect location with in a block you can find Starbucks, Whole Foods, Trader Joe's, Marianno's, Aldi and Goose Island Brewery plus many other stores and restaurants. Residential Street Parking permits are included for easy parking.brCheck out the Video in this listing for a full view! https://youtu.be/0xR2QJ_0w44

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Bath

Sleeps

Exceptional(16)

$594.08

/ Nightly

Private Vacation Home

Spacious Townhome! 3 bedrooms & 2 complete bath and 2 outdoor Patios, Near Train

Chicago, Illinois, United States

Spectacular Entire Townhome in the hearth of the city! 3 stories and 1900 sq feet of living space for guests with 3 bedrooms and 2 full bathrooms. Boasting TWO nice outdoor spaces. a lovely front patio and a very cute deck on the 3rd floor. Home is steps from the Train and just a 10 minute ride to downtown Millennium Park. My Townhome offers 1 King bed in the Master bedroom and 2 Queen beds in the additional bedrooms for sleeping up to 6 guests comfortably. Near grocery shop include Mariano's, Whole Foods, Trader Joe's and Aldi, Shopping, great restaurants, Theaters, the Chicago Zoo and everything Chicago offers. Parking permits are included for easy parking. brCheck out the video for a full view: https://youtu.be/0xR2QJ_0w44

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Sleeps

$241.17

/ Nightly

Private Vacation Home

3-bedroom house in beautiful Chicago with AC —— Pet friendly

Chicago, Illinois, United States

This superb house in Chicago offers 3 cozy bedrooms with a mix of queen, full, and king beds. The living room provides additional space with a comfy sofa bed for extra guests. Guests can relax in the soothing ambiance of this home, complete with AC, heating, and a hair dryer for convenience. Only a short distance from the city's attractions, this awesome property is the ideal retreat for your Chicago getaway. Enjoy your time in Chicago at our house.

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Bath

Sleeps

Exceptional(3)

$492.27

/ Nightly

Private Vacation Home

Cozy 5BR Chicago Retreat Sleeps 10

Chicago, Illinois, United States

Winter SpecialbrWelcome to your spacious and comfortable Chicago retreat — perfect for families, business travelers, travel nurses, relocation stays, and extended visits.brbrThis fully furnished 5-bedroom, 3-bathroom home comfortably accommodates up to 10 guests and is conveniently located near the Obama Presidential Center, Hyde Park, Woodlawn, major hospitals including UChicago Medicine, the lakefront, and downtown Chicago.brbrDesigned for both short and long stays, the home offers the perfect combination of comfort, convenience, and space for larger groups and professionals visiting the city.brbrGuests enjoy:brbr✔ 5 spacious bedroomsbr✔ 3 full bathroomsbr✔ Fast WiFi for work and streamingbr✔ Smart TVsbr✔ Fully equipped kitchenbr✔ Washer & dryerbr✔ Comfortable living and dining spacesbr✔ Free street parkingbr✔ Optional garage parking available for additional conveniencebr✔ Quiet residential neighborhoodbrbrPerfect for:br• Travel nurses and healthcare professionalsbr• Corporate and work travelbr• Insurance displacement staysbr• Family vacations and reunionsbr• Extended winter staysbr• Group trips to ChicagobrbrLocated minutes from hospitals, universities, restaurants, shopping, downtown Chicago, and the lakefront, this home provides easy access to everything while offering a peaceful place to relax after a busy day.Winter Stay Special Available brMonthly and extended-stay discounts are available during winter months for qualifying bookings.brbrWhether you’re visiting Chicago for work, family, relocation, or leisure, this spacious home is designed to make your stay comfortable, convenient, and memorable.

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Bath

Sleeps

Exceptional(13)

$169.07

/ Nightly

Private Vacation Home

A Charming spacious Paxton Condo clean 2000 sq. ft.

Chicago, Illinois, United States

This Modern New construction Paxton Condo was completed in 2007. brSoon to be just 1 block from the NEW Tiger Woods Golf coarsebrThe unit has an open floor plan with the Kitchen over looking the Great Room. It's a bright and sunny space.brThis location is perfect... Excellent Expressway access. Walking distance to our beautiful Lake Front..brThe University Of Chicago Hospital is just 2.8 miles. The McCormick Convention center 6.8 miles.brHyde Park Dining and Shopping is 2.8 miles away.. A hop skip and jump to fine dining.. and the Harper Hyde Park Movie Theaters.br 12 minutes from Downtown Chicago.Is just a quick ride down our Beautiful Lake Shore drive.. just 2.5 blocks away.brDivvy bikes located at the corner of 67th street. Take advantage and ride down the beach.br And enjoy The best Skyline in the world.brbr

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Bath

Sleeps

Exceptional(11)

$230.74

/ Nightly

Private Vacation Home

Charming Home in Portage Park

Chicago, Illinois, United States

This cozy four-bedroom, two-bathroom home is ideally located near O’Hare Airport and downtown Chicago, offering convenience and comfort. Designed with simplicity and functionality in mind, it features an open living and dining area with hardwood floors and ample natural light. While not high-end, the home provides a warm and welcoming atmosphere, perfect for those seeking a practical and affordable space.brbrA perfect blend of suburban charm and city accessibility awaits!

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Rent a place that suits your needs

Condo

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Sleeps

Vacation Home Rentals By Owner In Chicago, IL

$283.38

$278.03

$319.36

$193.47

$1006.25

$531.35

$1058.95

$409.04

$246.89

$174.66

$182.47

$489.57

$1360.22

$1838.55

$609.01

$594.08

$241.17

$492.27

$169.07

$230.74

Rent a place that suits your needs

Most popular vacation rentals in Chicago

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